Experience

Mark A. Singh

Senior Solutions Engineer • Technology Advisor • Customer & Engineering Advocate

More than two decades helping organizations understand, adopt, support, and evolve technology — from enterprise infrastructure and observability through cybersecurity, cloud transformation, and artificial intelligence.

Professional Reputation

Consistent Themes Across Public Work

Independent searches of my public professional footprint consistently identify the same themes.

Technical Educator

Recognized through webinars, workshops, technical demonstrations, public presentations, and product education.

Trusted Advisor

Frequently positioned between customers, engineering teams, product organizations, and business stakeholders to create shared understanding.

Product Advocate

Represented products publicly through conferences, workshops, trade shows, analyst engagements, webinars, and demonstrations.

Technical Translator

Known for translating technical complexity into actionable outcomes across support, engineering, product, sales, and customer-facing functions.

Career Summary

Senior technology professional with experience spanning enterprise infrastructure, observability, cybersecurity, customer success, technical leadership, product collaboration, and business alignment.

Built a career operating between customers, engineering organizations, product teams, and business stakeholders — helping organizations navigate technology adoption, modernization initiatives, operational challenges, and complex technical decisions.

Public-facing experience includes technical webinars, customer workshops, trade shows, analyst engagements, technical writing, executive presentations, and industry conferences throughout North America.

Career Themes

Customer Understanding

Understanding customer reality before proposing solutions, built through enterprise support, escalation management, renewals, workshops, and pre-sales engagements.

Technical Translation

Bridging customers, engineering, product teams, and business stakeholders through clear communication and shared understanding.

Technology Adoption

Helping organizations navigate major technology shifts from client/server systems through cloud, security modernization, observability, and AI.

Professional Experience

Gallivanting Travel & Independent Projects

Founder • 2023 – Present

• Exploring guided intelligence, AI-assisted workflows, and structured decision-support systems.
• Designing customer experiences focused on clarity, guidance, and workflow orchestration.
• Applying modern AI technologies to operational and customer-facing business processes.

iboss

Field Sales Engineer • 2022 – 2023

• Supported SASE, Zero Trust, and cloud security modernization initiatives.
• Led technical discovery, demonstrations, architecture discussions, and solution validation.
• Worked with organizations evaluating cloud-delivered security architectures and secure access models.

Progress Software

Senior Solutions Engineer • 2018 – 2022

• Led technical discovery, demonstrations, workshops, proof-of-concepts, and customer advisory engagements.
• Supported enterprise, healthcare, federal, financial services, and regulated environments.
• Recognized as a public-facing technical resource through webinars, Tech Field Day, customer events, and industry conferences.
• Selected by marketing leadership to represent products throughout North America.

Ipswitch, Inc. / Progress Software

Scale, Adoption & Customer Advocacy

Senior Escalation Engineer & Technical Leadership Roles • 2008 – 2018

As the organization matured, my role evolved from direct R&D interaction toward enterprise escalation management, customer retention, product adoption, knowledge strategy, and cross-functional collaboration.

Much of the work focused on helping customers achieve successful outcomes while balancing technical realities, product limitations, business expectations, and long-term relationships.

• Served as senior escalation authority for enterprise customer environments.
• Authored more than 60% of WhatsUp Gold knowledge base and training content.
• Reduced support case generation by approximately 35% through customer education initiatives.
• Achieved approximately 75% customer retention while assisting at-risk accounts and renewal conversations.
• Led support readiness and knowledge transfer following MOVEit and Dorian acquisitions.

Ipswitch, Inc.

Foundation Years — R&D Embedded Leadership

Technical Support Team Manager • 2002 – 2008

Shortly after joining Ipswitch, I was promoted into a Team Lead role and became part of the customer-to-engineering information flow connecting support, development, QA, documentation, product management, and engineering leadership.

At the time, I assumed this level of proximity to product development was normal. Only later did I realize how unusual it was for technical support to operate inside a Research & Development organization rather than outside of it.

My role extended beyond technical troubleshooting. I helped establish investigative workflows, escalation processes, defect triage practices, and communication frameworks that translated customer experiences into actionable engineering intelligence.

• Promoted to Team Lead within four months.
• Helped establish support processes during Ipswitch's migration into an R&D-centered support model.
• Served as a Voice of Customer representative within product development workflows.
• Worked directly with development, QA, documentation, and product management teams.

Ecommerce Systems Administration

Systems & Network Administration • 1998 – 2000

• Supported desktop, server, messaging, and network infrastructure.
• Administered IMail messaging environments.
• Developed foundational expertise in systems administration and enterprise operations.

United States Army

Automated Logistical Specialist 92A • 1994 – 1998

• Served with the 513th Military Intelligence Brigade.
• Supported NATO operations associated with Bosnia.
• Developed foundations in logistics, accountability, teamwork, and operational discipline.

Professional Toolkit

Customer Engagement & Technical Education

Webinars • Demonstrations • Workshops • Technical Writing • Public Speaking • Executive Presentations

Product & Engineering Collaboration

Jira • TestTrack • Agile • Defect Triage • Voice of Customer Programs • Cross-Functional Leadership

Customer Lifecycle & Operations

Salesforce • Sage CRM • ServiceNow • Renewals • Customer Retention • Technical Discovery

Infrastructure & Security Technologies

WhatsUp Gold • WS_FTP Server • VMware • Microsoft SQL Server • Azure • IIS • Infrastructure Monitoring

Public Recognition & Industry Presence

• Featured presenter at Tech Field Day.
• Hosted official Progress Software webinars.
• Authored technical content and knowledge resources.
• Represented products at customer workshops, trade shows, public sector events, and industry conferences.
• Selected by marketing leadership for public demonstrations, partner enablement, and channel-facing technical events.

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